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Somewhere between the Green Mountains and White Mountain National Forest, on I-91, we found ourselves nestled in the early morning fog, the fall foliage hanging onto limbs, as the sun began to peek its rays through the early morning sky. That’s when I knew we had made one of the best trips of our lives happen.
My sister and I have always had an affinity for the East Coast, but we never knew how magical it would be in the fall season. We started our trip in Vermont, made our way down the Rhode Island coastline and up to Boston. Along the way, we made a pit stop or two, met up with our best friends, and experienced what the middle of October felt like in New England. It was truly the best sister getaway that will live rent-free in our minds forever.
Today, I’m breaking down every city we visited, the food stops worth making, and the activities we ventured to do along the way. Keep reading to see the full itinerary, so you can maybe add some to-dos to your next trip to New England.
The Map of New England Road Trip
Day 1: Flew into Burlington, Visited Stowe & Drove to Newport, VT
After a full travel day and connecting flights, we made our descent into Burlington, VT and immediately saw the changing leaves. Burlington has a lot of fun shops and stops, and we wish we had more time to explore the area, but we were planning to meet a friend in Newport.
We rented a car with Avis, and you can get a discount with them if you have an Amazon Prime account. At this time, Avis car rentals were significantly cheaper than other competitors and were so easy to schedule, pick up, and drop off.
We hopped in the car and started our journey up north to Newport. Along the way, we had to stop through Stowe and visit the Cold Hollow Cider Mill. We browsed around the store and took hot apple cider and apple cider donuts to go. PSA: It’s super busy during peak season — especially on the weekends, so plan your time accordingly.
After grabbing a drink and a snack, we drove up to Newport through winding roads as the sun set. We got to see so many gorgeous countryside towns and take in the fall foliage.
Day 2: Went to Shattuck Hill Scenic Overlook and Visited Burtt’s Apple Orchard
We woke up in Newport, where our best friend lives. She showed us around the small town, and we were amazed by the beauty. There are mountain ranges and hills all around, and the town is situated on a large lake. In fact, as we looked across the lake from Shattuck Hill Scenic Overlook, we could see where Canada began.Â
Next on the agenda was a trip to Burtt’s Farm and apple orchard. We had never visited an apple orchard before, so this was such a fun experience. There’s just something about picking your own apples that truly makes it feel like fall.
We grabbed some hot apple cider and a donut as a snack, and headed back to our friend’s house where we made an apple pie with the apples we picked.
Day 3: Stopped in Woodstock, VT and Drove to Newport, RI
This was our biggest travel adventure day yet. We reluctantly and sadly left our friend’s house bright and early to start our trip down to Newport, RI. But first, we had to make a stop in Woodstock.
As we drove south on I-91 through New Hampshire and Massachusetts, through the trees we saw beautiful slightly-past-peak colors on the trees. The fog was really dense in areas, but when the sun poked its rays through, the views were gorgeous.
After an hour and a half, we had made it to Woodstock, VT. The only way to describe it this time of year is like a picturesque fall Hallmark movie. The trees have gorgeous color; there are historical buildings all around, wooden buildings (that are perfect for taking pictures. There are so many wonderful shops to stop into also. While we could probably name them all, here are a few worth visiting:
- Farmhouse Pottery: Stunning Pottery & Seasonal Decor
- Mon Vert Cafe: Coffee
- The Woodstock Gallery: Stunning collection of artworkÂ
- Mountain Ave Bridge: Perfect for taking pictures
- Woodstock Inn & Resort
- The Normal Williams Public Library
- Farmer & The Bell: Bakery & Cafe only open Thursday-SundayÂ
Next, we drove down to Newport, RI. It was about a 4-hour drive down to the coast. We made it to The Carriage House Inn. The staff was welcoming and nice. However, the location of the Inn was a bit farther away from downtown than we would have liked. Next time, we will book an inn closer to the wharf marina.Â
We ate dinner at Giusto, and this was probably the best seafood we both ate during the trip. We ordered the Sourdough Crostini, the Calamari Salad, and the Local Fish. It tasted so fresh, light, and modern. It was just what we needed after a long travel day. Not to mention, the coastal charm was refreshing to take in.
After dinner, we walked down Thames Street and got ice cream at Sticks and Cones.
Day 4: Cliff Walk, Nitro Bar, Kiel James Patrick & Drive to Boston
The next morning we woke up at 6:00 am to walk to the Cliff Walk trail that runs along the coast. This may be one of the most infamous activities to do in Newport, because you get a scenic view of the ocean on one side and a tour of the historic mansions on the other.
After venturing halfway down the trail, we turned towards town to get breakfast. We stopped at The Nitro Bar and got the Whipped Maple Sea Salt Latte, coffee cake, and avocado toast. I have to say, we were both absolutely SHOOK at how delicious the coffee was. I think it was the best coffee I’ve ever had, and it made me want to move to Rhode Island immediately — just to have it close by.Â
After breakfast, we walked over to the Kiel James Patrick store, browsed their adorable sweaters, and bought a couple of items to take home. It was such a gorgeous store. Side note: they rotate their sweaters out every season, which makes it a must- see destination spot all year round.
After a bit of shopping, we checked out of our hotel and drove to Boston.
We dropped our rental car off at Boston Logan Airport and took the bus to our hotel. (We knew that our form of transportation around Boston would be walking, train, and bus, so we didn’t need the car anymore.)
We stayed at the Citizen M Back Bay Hotel and were unexpectedly upgraded to a larger corner room with a view of the Boston Red Sox baseball field — INSANE! We loved this hotel so much, and everyone was so nice.Â
The front doors of the hotel spit you right out onto Newbury Street, which is a hub for shopping and college life.
We walked through the Boston Common to go to dinner in the North End. We ate at the cozy Florentine Cafe, ordered Bolognese and a Caesar Salad, and planned the next day’s activities. On our way back to the hotel, we stopped into the Modern Bakery and got a few Italian pastries to share.
Day 5: Tatte, Beacon Hill Books, Paul Revere’s House, Shopping, Saltie Girl
This was our only full day in Boston, so we packed in a bunch of different things.
There are Tatte Bakery & Cafe locations all over the city, which makes it easy to stop in for breakfast and coffee. They have a beautiful display of pastries to choose from too.
Next, we walked through the commons to Beacon Hill Books. It’s such a magical place to visit. With three floors of book displays, there’s something everyone in the family can enjoy. Plus, it’s worth stopping into their cafe below the store.
While you’re in Beacon Hill, check out all the adorable gift shops and maybe purchase a souvenir to take home.
Then, we walked over to the iconic Acorn Street, which is a popular place to take pictures in the fall. It’s also fun to walk around the neighborhood and look at Halloween decorations too.
After that, we walked back up to the North End to look in some shops and see Paul Revere’s house. If you have time, they conduct tours throughout the day.Â
However, by this time, we were hungry for lunch, so we stopped in Florina Pizza to get a slice of pepperoni and cheese pizza. We sat in the Boston Common to eat and people-watch. It’s always so relaxing after walking all morning.
In the afternoon, we shopped on Newbury Street. This street is packed with some of our favorite stores like Maxwell, J.Crew, Max Mara, Mejuri, Varley, and so many more.
For dinner, we made reservations at Saltie Girl — a highly recommended seafood restaurant in the area. The atmosphere was so cute, and the food was so delicious as well.
Day 6: Boston Red Sox Field, Bagels, Boston Tea Party Museum, Boston Public Library
On our last half day in Boston, we woke up early, walked past the Boston Red Sox baseball field, and grabbed a bagel sandwich at Brick Street Bagels.
Then we headed over to see the Boston Tea Party Museum. If we had more time, we totally would have added this to the list.
Then, we hopped over to a couple of shops to grab some gifts to bring home for our family and ended the day at the Boston Public Library.
Other Boston Food Stops to Try:
- BON Coffee and Matcha: BEST Matcha in Boston
- Blank Street
- Tatte Bakery & Cafe
- Mike’s Pastry
- By Chae Matcha
